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It was opened in 1852 as a mixed prison, but due to growing demand for space for female prisoners became female-only in 1903. Prisoners included Kitty Byron and suffragettes such as Anne Miller Fraser, Constance Markeivicz, Charlotte Despard, Mary Richardson, and Hanna Sheehy-Skeffington. Norah Elam had the distinction of being detained during both World Wars, three times during 1914 as a suffragette prisoner under the name Dacre Fox, then as a detainee under Defence Regulation 18B in 1940, when she was part of the social circle that gathered around Diana Mosley during their early internment period. Later, after her release, Elam had the further distinction of being the only former member of the British Union of Fascists to be granted a visit with Oswald Mosley during his period of detention there with his wife Diana Mosley (née Mitford).[1]

The bodies of all executed prisoners were buried in unmarked graves within the walls of Holloway Prison, as was customary. In 1971 the prison underwent an extensive programme of rebuilding, during which the remains of all the executed women were exhumed. With the exception of Ruth Ellis, the remains of the four other women executed at Holloway (Amelia Sach, Annie Walters, Edith Thompson and Styllou Christofi) were subsequently reburied in a single grave at Brookwood Cemetery near Woking, Surrey

Holloway Prison was completely rebuilt between 1971 and 1985 on the same site. The redevelopment resulted in the loss of the "grand turreted" gateway to the prison, which had been built in 1851; architectural critic Gavin Stamp was later to regret the loss and to note that the climate of opinion at the time was such that The Victorian Society felt unable to object.[3]

In October 1999, it was announced that healthcare campaigner and agony auntClaire Rayner had been called in to advise on an improved healthcare provision at Holloway Prison. Rayner's appointment was announced after the introduction of emergency measures at the prison's healthcare unit after various failures.[4]

In September 2001, an inspection report from Her Majesty's Chief Inspector of Prisons claimed that Holloway Prison was "failing" many of its inmates, mainly due to financial pressures. However, the report stated that the prison had improved in a number of areas, and praised staff working at the jail.[5]

In March 2002, Managers at Holloway were transferred to other prisons following an inquiry by the Prison Service. The inquiry followed a number of allegations from prison staff concerning sexual harassment, bullying and intimidation from managers. The inquiry supported some of these claims.[6]

An inspection report from in June 2003, stated that conditions had improved at Holloway Prison. However the report criticised levels of hygiene at the jail, as well as the lack of trained staff, and poor safety for inmates.[7] A further inspection report in September 2008 again criticised safety levels for inmates of Holloway, claiming that bullying and theft were "rife" at the prison. The report also noted high levels of self-harm and poor mental health among the inmates.[8]

A further inspection in 2010 again noted improvements, but found that most prisoners said they felt unsafe, and that there remained 35 incidents a week of self-harm.[9] The prison's "operational capacity" is 501.[10]

Holloway Prison holds female adults and young offenders remanded or sentenced by the local courts. Accommodation at the prison mostly comprises single rooms, however there is some dormitory accommodation.

One of the characters in the 1997 Canadian sci-fi/horror movie Cube is named after Holloway Prison.

In Are You Being Served "It Pays to Advertise" (Season 5, episode 7) Mrs. Slocum says, when talking about her false eyelashes, "It is like looking through bars, I might as well be in Holloway."

In the Thames Television series "Rumpole Of The Bailey" episode "Rumpole And The Alternative Society", the girl who Barrister Horace Rumpole was defending in Court until she admitted her guilt to him, was sentenced to 3 years at HM Holloway Prison.

In the classic series Upstairs, Downstairs, the second season episode A Special Mischief has Elizabeth Bellamy joining a band of suffragettes whence they go out one night vandalising wealthy homes. Rose, the parlormaid, follows Elizabeth and her suffragette friends when they are apprehended by the police. Rose is mistakenly thought to be a suffragette and is put in a ladies' prison (Holloway is very much implied). Elizabeth is spared going to jail as her bail is paid for by Julius Karekin, one the rich men being vandalised by the suffragettes. Elizabeth and her new rich boyfriend Julius Karekin bale Rose out of prison.[11]

In the BBC One series Call the Midwife, the third season episode three set in 1959, Sister Julienne and Midwife Trixie go to the prison to provide medical care to three pregnant inmates who have gone without treatment for a while. As part of their medical care Sister Julienne and Midwife Trixie advocate for less manual labour and more rest for the pregnant women. In addition to healthcare, Sister provides support and the means for one woman to keep custody of her child after her release.

In the German TV 1966 crime drama Das ganz grosse Ding, from a script by Victor Canning, the main character, Dickie Gray, is shown being released from Holloway Prison. Clearly the German director did not know that it was a women's prison at that time.